Bookkeeping Questions to Ask an Accountant

The most useful questions to ask an accountant are about your own books: whether they are set up correctly, where the cash is going, which expenses you are recording wrong and what will be a problem at tax time. A single session can fix mistakes that compound for years. This guide gives you the questions by topic, explains who you should be asking, and shows what to prepare so you can get expert advice online and leave with a clean list of fixes.

Bookkeeper, accountant or CPA?

These titles are used loosely, so ask what the person actually does:

Role	What they do	Licensed?
Bookkeeper	Records transactions, reconciles bank accounts, produces basic reports	No license required in most states
Accountant	Reviews the books, prepares financial statements, advises on structure and cash flow	Not necessarily
CPA (Certified Public Accountant)	Licensed accountant who can also advise on tax, represent you before the IRS and sign certain reports	Yes, by state board

For getting your books in order, a bookkeeper or accountant is often enough. For tax strategy, audits or anything where a signature carries weight, you want a CPA. You can check a CPA's license with your state board of accountancy; most boards have an online lookup.

This article is general guidance. It is not a substitute for a licensed professional who has seen your actual numbers.

Questions about your books and software

Start here if you are not confident your records are right:

1. "Is my chart of accounts set up sensibly for my type of business?" Too many categories make reports useless; too few hide problems.
2. "Should I be on cash or accrual basis?" This changes when income and expenses are recorded. Which is right depends on your business, and the choice affects your taxes, so an accountant should confirm it.
3. "Which software fits my size, and am I using it correctly?" Most small businesses use one of a few cloud tools. The common mistake is not the tool but the setup: bank feeds that are not reconciled, duplicate transactions, invoices marked paid twice.
4. "What does my balance sheet say that my profit and loss does not?" Many owners only look at profit. The balance sheet shows debt, what customers owe you and whether the business could survive a slow month.
5. "What should I check every month, and how long should it take?" A good answer is a short routine: reconcile accounts, review unpaid invoices, compare this month to last.

Questions about cash flow

Profitable businesses still run out of cash. These questions find the gap:

• "Why is my profit up but my bank balance down?" Usually inventory, loan repayments, owner draws or customers paying late.
• "How many days do customers take to pay me, and how do I shorten it?" Ask about deposits, shorter terms and automated reminders.
• "How much cash should I keep in reserve?" The answer depends on how predictable your sales are, but a target in months of expenses is more useful than a vague "more."
• "Can you help me build a 13-week cash flow forecast?" This simple tool shows cash in and out each week for the next quarter and is the single most useful report many small businesses never produce.

A worked example: a landscaping business showed a $40,000 profit for the year but could not make payroll in March. The accountant found that customers were averaging 55 days to pay and the owner had bought two trucks in cash. The fix was deposits on new jobs and a small equipment loan to spread the cost. Nothing about the business changed except timing.

Questions about expenses and records

Expense mistakes are what make tax time painful, so these are the questions to ask an accountant before the year ends:

• "Which of my expenses am I categorizing wrong?" Meals, travel, home office, vehicle and equipment are the usual trouble spots.
• "What counts as a business expense versus a personal one, and how do I keep them separate?" The practical answer starts with a dedicated business bank account and card.
• "What records do I need to keep, and for how long?" The IRS publishes recordkeeping guidance for small businesses; your accountant can tell you how it applies to you.
• "Should this large purchase be expensed or depreciated?" The treatment affects your tax bill over several years.
• "Do I need to send 1099 forms to any contractors I paid?" Ask before January, not after.

If you are self-employed rather than running a company with staff, the same questions apply, with home office and vehicle use being the ones most often recorded wrong.

What to prepare before the call

Send these a day or two ahead so the session is spent on answers:

1. Read-only or accountant access to your bookkeeping software, or exported profit and loss, balance sheet and bank transactions for the last six to twelve months
2. A list of what feels wrong or confusing
3. Your biggest three expenses and biggest three customers
4. Any notices from the IRS or your state
5. The one decision you need help with, such as whether to hire, buy equipment or change structure

Never share your bank login. Accounting software has a built-in way to give an accountant limited access, and that is what you should use. Our guide to accounting advice online covers how a remote session works in practice.

When to get ongoing help

One session is enough to find and fix setup problems. You probably need regular help when:

• You cannot keep up with monthly reconciliation yourself
• You have employees or sales tax in more than one state
• Revenue is growing fast and decisions depend on current numbers
• You are preparing to raise money, apply for a loan or sell the business

Even then, start with a single session. Use it to decide what you can do yourself with a monthly routine and what genuinely needs a professional. You can book an accountant or bookkeeper on ConsultChat; payment is held by the platform until the session is delivered, and reviews come only from completed sessions.

Before you book, read our list of questions to ask before booking a consultant, then add the questions to ask an accountant from this article that match your situation. Three well-chosen questions will do more for your books than twenty general ones.